And in the 54th minute, the answer came. The Red Stars scored the game's only goal when Dani Colaprico blasted in a rebound of her own shot into the upper 90. The goal held up for a 1-0 Chicago victory, but it could have been much worse.
But 1-nil win was the final result in Illinois as Chicago had its World Cup sendoff game for Christen Press, Shannon Boxx, Julie Johnston and Lori Chalupny played its final game for the hosts before flying to Los Angeles for training with the US National Women's Team for June's World Cup.
The win put Chicago in a tie for first in the National Women's Soccer League (NWSL) with Portland with seven points each.
By contrast, Sky Blue FC was trying to replace half their backline with US National Women's Team defenders Christie Rampone and Kelley O'Hara in national team camp.
The defense bent but never broke for much of the game, especially in the first half when the home team had an 11-2 shot advantage with a 4-0 shots-on-goal advantage. Goalkeeper Brittany Cameron was especially resilient with two monster saves in each half - one on Press, the other off Chalupny.
Press was especially active in the first half, all over the field with seven of the 11 shots but many were or off target.
Chalupny had the best chance of the opening half when she made an overlapping run and send to the far post but it rolled wide.
Chicago scored when Vanessa DiBernardo sent a driving corner kick to the far post. Boxx headed into the mix and Colaprico left-footed a shot that bounced off the head of Johnston. The rebound landed at Colaprico's foot and she made no mistake putting into the upper left corner.
The goal came after Sky Blue FC has come out in the opening minutes of the second half determined to possess a little more. The distribution began to open up play, especially with midfielder Shawn Gordon changing the point of attack.
Minutes after the goal, Nadia Nadim nearly got on the end of a Katy Freels service but Canadian international goalkeeper Katrina LaBlanc stymied the effort.
The next best opportunity came in the final minutes when reserve Lo'Leu LaBonta headed as corner kick from Freels that just went wide.
Sky Blue FC returns home for a Saturday match versus Seattle.